2-Chloro-1,1-dimethoxyethane → HCID 20443243, compound

HRID 2418013Notes

Reaction equation

HRID 2418013 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4]S.COC(OC)CCl.[Na].[CH2:16]([SH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([S:23][C:3]([O:6][CH3:7])([O:2][CH3:1])[CH3:4])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 609862-Chloro-1,1-dimethoxyethaneHCID 148182602,2-Dimethoxyethane-1-thiolHCID 86739628HCID 86739628, compound

Product 1

HCID 20443243HCID 20443243, compound

Procedure

Several processes for making 2-mercaptoacetaldehyde dimethylacetal (I, R1 =R2 =CH3) are reported by Parham et al., J. Am. Chem. Soc. 75, 2065-2069 (1953). These processes involve reaction of 2-chloroacetaldehyde dimethyl acetal with (1) benzylmercaptan sodium salt to produce benzyl-(1,1-dimethoxy ethyl)sulfide which was then reduced with sodium/ammonia to the desired acetal; (2) sodium sulfide to form 1,1,1', 1'-tetramethoxyethyl disulfide followed by reduction of said disulfide using sodium/ammonia or lithium aluminum hydride; and (3) sodium polysulfide to give a mixture of polysulfides which was reduced with sodium/ammonia. A fourth process described in said reference comprises the action of potassium hydrosulfide on diethyl or dimethyl bromoacetal to produce the corresponding dialkyl mercaptoacetal.

Sources & evidence

ORD record
ord-4ac2a633639b41a68d5d1d0e0233179d
Source dataset
uspto-grants-1984_09
Patent number
US04471139

Reaction notes

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