Hydrochloric Acid → 2-(Dimethoxymethyl)-6-hydroxy-2,5,7,8-tetramethyl-chroman

HRID 462584Notes

Reaction equation

HRID 462584 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[C:4]1([CH3:19])[CH2:13][C:12](=O)[C:11]2[C:6](=[C:7]([CH3:18])[C:8]([CH3:17])=[C:9]([OH:16])[C:10]=2[CH3:15])[O:5]1.[BH4-].[Na+].[OH-].[Na+].Cl>CO>[CH3:21][O:20][CH:3]([O:2][CH3:1])[C:4]1([CH3:19])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH3:18])[C:8]([CH3:17])=[C:9]([OH:16])[C:10]=2[CH3:15])[O:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 130515362-(Dimethoxymethyl)-6-hydroxy-2,5,7,8-tetramethyl-chroman-4-one

Product 1

HCID 130515422-(Dimethoxymethyl)-6-hydroxy-2,5,7,8-tetramethyl-chromanYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.4 g (32 mmoles) of the product from Example 2 were reacted with 2.43 g (64 mmoles) of NaBH4 in 100 ml of methanol at 20°-60° C. After 6 hours, a further 2.43 g of NaBH4 were added, after which the reaction mixture was stirred at room temperature for 16 hours. 100 ml of 3N NaOH were then added, and the mixture was neutralized with dilute hydrochloric acid and then extracted with ether, a brown oil being obtained as the crude product in 95% yield. IR: 3,600 (broad) cm-1.

Workup

  1. extractionextracted with ether

Sources & evidence

ORD record
ord-8fccdebae2d64e789f4a336ee65d77df
Source dataset
uspto-grants-1985_05
Patent number
US04515975

Reaction notes

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