Methanol → 6-(7-Hydroxyheptyl)-7-(3-hydroxy-3-methyloct-1-enyl)-1,4-dioxaspiro[4,4]nonane

HRID 372056Notes

Reaction equation

HRID 372056 reaction equation
CO.O.[OH:4][C:5]([CH3:34])([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:6]=[CH:7][CH:8]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH:9]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][Si](C)(C)C>C(O)(=O)C.C(OCC)C>[OH:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:9]1[CH:8]([CH:7]=[CH:6][C:5]([OH:4])([CH3:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:16][CH2:15][C:10]21[O:14][CH2:13][CH2:12][O:11]2

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 537744147-(3-Hydroxy-3-methyloct-1-enyl)-6-(7-trimethylsiloxyheptyl)-1,4-dioxaspiro[4,4]nonane

Product 1

HCID 570707516-(7-Hydroxyheptyl)-7-(3-hydroxy-3-methyloct-1-enyl)-1,4-dioxaspiro[4,4]nonaneYield 78.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

Methanol (30 ml.), water (15 ml.) and glacial acetic acid (3 drops) were added to 7-(3-hydroxy-3-methyloct-1-enyl)-6-(7-trimethylsilyloxyheptyl)-1,4-dioxaspiro[4,4]nonane (0.5 g.) and the mixture was stirred at room temperature for 30 minutes. An excess of diethyl ether was then added and the resulting solution was washed with dilute aqueous sodium bicarbonate solution and sodium chloride solution respectively, and dried over sodium sulphate, to give crude 6-(7-hydroxyheptyl)-7-(3-hydroxy-3-methyloct-1-enyl)-1,4-dioxaspiro[4,4]nonane (0.33 g.), νmax 3400 cm-1, pure enough to use in the next stage.

Workup

  1. washthe resulting solution was washed with dilute aqueous sodium bicarbonate solution and sodium chloride solution respectively
  2. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-24b446fafe974818890826487e02f47c
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

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