N,N-Dimethylaniline → 2,6,10,10-Tetramethyl-1-oxa-spiro[4.5]dec-6-yl butyrate

HRID 46610Notes

Reaction equation

HRID 46610 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][C:4]2([C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH2:8][C:7]2([CH3:15])[OH:14])[O:3]1.CN(C)C1C=CC=CC=1.[C:25](Cl)(=[O:29])[CH2:26][CH2:27][CH3:28]>>[C:25]([O:14][C:7]1([CH3:15])[CH2:8][CH2:9][CH2:10][C:11]([CH3:13])([CH3:12])[C:4]21[O:3][CH:2]([CH3:1])[CH2:6][CH2:5]2)(=[O:29])[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 8855Butyryl chlorideHCID 6542853398-90-6

Product 1

HCID 233465732,6,10,10-Tetramethyl-1-oxa-spiro[4.5]dec-6-yl butyrateYield 57%

Procedure

2.12 g (0.01 M) of 2,6,10,10-tetramethyl-1-oxa-spiro[4.5]decan-6-ol -- isomer A; see Example 1 -- were treated with a mixture of 12.1 g (0.1 M) of N,N-dimethylaniline and 5.3 g (0.05 M) of butyryl chloride as indicated in Example 3 -- except heating at 100° for 3 hours -- to give 1.6 g (57%) of the desired ester, b.p. 120°/0.5 Torr.

Workup

  1. temperatureexcept heating at 100° for 3 hours

Sources & evidence

ORD record
ord-141d94c2739a4d6cba6b6beafc04e872
Source dataset
uspto-grants-1979_11
Patent number
US04174327

Reaction notes

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